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If there's one thing an NHL team doesn't want when it signs a contract – especially a long-term contract – it's regret.

Darcy Tucker. Jason Blake. Jeff Finger. Mike Komisarek. Colton Orr. Luke Schenn. Mikhail Grabovski. John-Michael Liles. Joffrey Lupul. David Clarkson. Phil Kessel (the second time). Dion Phaneuf.

That's almost all of the four-plus year contracts the Toronto Maple Leafs have signed in the eight seasons under previous management regimes, and they almost all ended poorly. Buyouts. Demotions. Salary-dumping trades.

Nothing kills you in the NHL's salary-cap system like bad money, and the Leafs have had loads of it over the years.

These new deals for Morgan Rielly and Nazem Kadri won't be added to the list.

It's not just that paying Rielly $5-million a season and Kadri $4.5-million a season until 2022 is fair-market value. It is. What's also important is the Leafs are finally paying it to homegrown young players who still have room to get better.

You look at that list above, and the average age of those dozen players when they started playing on their long-term deals in Toronto was 29. Schenn was the only really young player.

Rielly turned 22 last month. Kadri is only 25, even though it feels like he's been around forever (since the 2009 draft).

As the richest team in the game, the Leafs have made a lot of bad bets over the years. None was worse than hefting huge money at all those beaten-down veterans. In almost every case, Toronto was buying unrestricted free agency years at a premium and getting a declining asset for many declining years.

You can sell that if you're a contender, as with Anaheim gambling on stars, such as Ryan Getzlaf, Corey Perry and Ryan Kesler. Try to win a Cup, pay for it later.

The Leafs were never close, and they did it anyway – often for secondary players.

But the NHL is more of a young man's league than it's ever been. It's faster and smarter and methodical, to the point most front offices realize players are peaking at 23 or 24 – not 29. The Leafs missed a lot of trends in the first decade of the salary cap, but new management, led by president Brendan Shanahan, has caught on to this one. This whole season, in fact, starting with moving Kessel to Pittsburgh last July, has been out with the old and in with the youth.

When it has made sense, they've bet on it, as when Jake Gardiner got his five-year deal in the summer of 2014.

Now, Rielly and Kadri.

"There's more that they can do," Leafs GM Lou Lamoriello said shortly after the deals were announced on Wednesday morning. "All you have to do is look at the age where they're at. There's no question they have a level that they haven't reached yet."

With Rielly, you could almost see the improvement week-to-week and month-to-month this season. His minutes kept increasing and, when partner Matt Hunwick went down, so did his underlying numbers such as puck possession.

Leafs coach Mike Babcock dealt Rielly an almost ridiculously heavy load for a third-year defenceman, without a strong partner, often without power-play minutes and often on an overmatched Toronto team.

There were tough nights, but at minimum, Rielly showed he will be a top-four defenceman in the NHL through his peak years, which are coming soon. And top-four defencemen who put up points – which he will – will get paid $5-million or more every year.

He's worth the money, even if you don't factor in Rielly's considerable attributes off the ice. This is a driven, humble and tireless kid who will excel under Babcock because he doesn't mind the intense push. He could even end up as the long-awaited captain, if his game continues to improve. He has the right mind for it.

The Leafs like Rielly so much they were believed to be willing to go seven or even eight years on this deal, which is another shift in philosophy. In the past, Toronto would pay its vets and nickel and dime the restricted free agents.

Now, they realize Rielly's price will only go up if they wait.

"I certainly don't want to go anywhere," Rielly said. "It's about being in Toronto, being a part of this and having belief in the team that's here and the time we have in place [to get better]."

Kadri is a completely different animal. He is older. He's had a more tortured road. He's not particularly humble, and he is likely getting close to his ceiling as a player – which is fine given he looked like a pretty good No. 2 centre tasked with being the No. 1 this season. (He only had 45 points, but he was dragging Michael Grabner around the ice many nights. And that low shooting percentage will come up.)

But all the praise Kadri received from Lamoriello and Babcock wasn't elaborate subterfuge. The old-school hockey types in Toronto's front office like his battle; the new-school ones love that he is so good with the puck that he always has it or is fighting for it.

The Leafs were lucky that Kadri wanted to stay. He hasn't been shy about wanting a long deal, and he took a discount on his UFA years – all four of them he signed for – in order to get it. While negotiations with Rielly's camp were somewhat arduous, they were downright easy with Kadri.

And, in the end, he will barely sneak into the top 50 centres in pay next year.

All this time, through the controversies and browbeating, what Kadri really seemed to want was someone in the organization to look at him and say "you know what, we want you around."

On Wednesday, they did.

"It means a lot to be rewarded," Kadri said.

It says something, too, that both players looked at the Leafs last-place season and signed up for a lot more. Like many of the young players in the organization, they have fully bought in to the idea that Shanahan and company know what they're doing and the best is coming.

These two contracts are more evidence they're right.